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@Jeroen said:
From another thread…

“Our free will is constrained by all manner of addictions and traumas, attractors and avoiders, old dreams and terrors. To call us ‘free’ would be a major stretch of the imagination.”
— me

So really a lot of the journey towards freedom is noticing where your mind is not free, and then making efforts to free it. At the same time a lot of impositions on our freedom take the form of burdens that we can choose to lay down, including society’s expectations of us having to be productive.

Free your mind first, then all other forms of freedom come easier.

Yes and no. I'd say yes that part of it is noticing where we're not free and making efforts to increase our freedom. So I would like general like to have more freedom in my day, to work less hours and have more free time to do the things I enjoy. I'd also like to be free mentally of some of the things that cause me suffering. And that journey requires a lot of work, from externally trying to change the world and the logic of current social relations to have the freedom to work less and still be able to live, to internally trying to change my mental habits to be free from attachments and wrong views that create suffering and dissatisfaction. And conventionally, I can say I want freedom of choice and freedom from suffering and privation.

Where I'm hesitant to agree is that there is a free will at all. What aspect of our volition (cetana) is free, unconditioned? This search is, again, like the search for the heartwood of a banana tree. You peel back layer after layer only to discover that it's ultimately "empty, void, without substance." This is purely speculative, but I don't think we have an aspect of the khandhas that's free, unconditioned. I think that the path can help condition us to act more skillfully, do less harm, understand causality to condition more happiness and less suffering (morality, kamma), and ultimately get us to a place where let go of craving and clinging and "touch the deathless" (awakening). What I think this means is that there's an aspect of consciousness that's primordial, fundamental, what the Buddha poetically refers to as:

'Consciousness without surface [vinnanam anidassanam],
endless, radiant all around,
has not been experienced through the earthness of earth ... the liquidity of liquid ... the fieriness of fire ... the windiness of wind ... the allness of the all.' (MN 49)

And this level of consciousness isn't conditioned, doesn't arise and cease, doesn't intend, etc. It's experienced when all craving and intentionality stops. It's not the same as our sensory experience of consciousness (vinnana-khandha), and it's not equivalent to a self or soul as it's not an individually existing thing unique to our being that drives us, but part of the fabric of reality itself (along with space-time). And looking back from this experience, we can see how all of our particular human experiences are conditioned, how they arise and cease, and we no longer cling to them with that same strength or imbue them with the same solidity as we once did.

In essence, you can't condition or create the unconditioned or even the experience of it, but you can condition an end to conditioning (a moment free from mental acts of attachment and intention), thereby opening up to the experience of the unconditioned already present and hidden in plain sight. Hence, as the Tao Te Ching says, the unwanting soul sees the hidden:

The way you can go
isn’t the real way.
The name you can say
isn’t the real name.

Heaven and earth
begin in the unnamed:
name’s the mother
of the ten thousand things.

So the unwanting soul
sees what’s hidden,
and the ever-wanting soul
sees only what it wants.

Two things, one origin,
but different in name,
whose identity is mystery.
Mystery of all mysteries!
The door to the hidden. (Le Guin)

Or as the Buddha put it:

"For a person who knows & sees things as they actually are, there is no need for an act of will, 'May I feel disenchantment.' It is in the nature of things that a person who knows & sees things as they actually are feels disenchantment.

"For a person who feels disenchantment, there is no need for an act of will, 'May I grow dispassionate.' It is in the nature of things that a person who feels disenchantment grows dispassionate.

"For a dispassionate person, there is no need for an act of will, 'May I realize the knowledge & vision of release.' It is in the nature of things that a dispassionate person realizes the knowledge & vision of release. (AN 11.2, Thanissaro)

There's a level of reality that's intellectually unknowable to us, and we must paradoxically submit to the unknown, rest in it, become one with it by being able to let go of what isn't ours. In some sense, we're powerless because there's a limit to our agency, to what we can will and achieve in this world. We are not free from causality. "When this is, that is. From the arising of this comes the arising of that. "When this isn't, that isn't. From the cessation of this comes the cessation of that" (MN 38).

And the lesson for us to somehow learn is that, to achieve a glimpse of ultimate reality, we must set aside all desires and grasping and acts of will, and in the midst of that silent awareness free from our normal experience of space and time and sense of self, we can touch the deathless and become liberated. The unknown is thus known, not through our intellect or striving or act of will, but through a direct experience of, dare I say, divine emptiness in the depths of our heart. Something quite difficult yet effortless to achieve if the conditions are right.

OP, I've heard recently a teaching on two freedoms and how they are not the freedom offered by Dharma. There is freedom from and freedom to. Freedom from x, y, z. In a way a lot of what we do is try to attain freedom from oppression, from our traumas, from even suffering. Or freedom to x, y, z. Freedom to live a good life. Freedom to do whatever we want to. Dharma offers a freedom that isn't from or to.

This teaching that was impressed upon me really shocked me because pretty much everything I do is well for those two modes of freedom. And even my dharma practice is about getting freedom from suffering and freedom to live a fuller life. But freedom in the dharma is something else entirely.

And thus I am presented with two things. My spiritual materialism and something so radical that my conventional mind cannot make sense of it.